Sodium Hypochlorite → HCID 86685714, compound

HRID 1055275Notes

Reaction equation

HRID 1055275 reaction equation
[O:1]=[C:2]1[NH:6][CH2:5][CH2:4][N:3]1[CH2:7][CH2:8][O:9][C:10]1[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=1[CH:12]=[N:13][OH:14].[O-]Cl.[Na+]>C(Cl)Cl.O>[O:1]=[C:2]1[NH:6][CH2:5][CH2:4][N:3]1[CH2:7][CH2:8][O:9][C:10]1[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=1[C:12]#[N+:13][O-:14]

Participants

5

Reactant 2

HCID 23665760Sodium HypochloriteHCID 86685713HCID 86685713, compound

Product 1

HCID 86685714HCID 86685714, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-18 °C

Procedure

To a suspension of 2-[2-(2-oxoimidazolidin-1-yl)ethoxy]benzaldehyde oxime (20.2 g, 0.081 mol) in CH2Cl2 (400 mL) at −1° C. is added, dropwise over 10 minutes, an aqueous NaOCl solution in water (157 mL, Aldrich, >4% of active chlorine). The reaction medium is then stirred for 20 minutes. The aqueous and organic phases are separated and the aqueous phase is extracted with CH2Cl2 (twice 75 mL). The combined organic phases are washed with water (3 times 10 mL) and dried over Na2SO4. The phases are concentrated to 100 mL under reduced pressure at room temperature. 50 mL of petroleum ether are added. The solution is cooled to −18° C. (3 hours). The precipitate is filtered, washed with CH2Cl2/petroleum ether (5 mL/10 mL; then 5 mL/20 mL; then 0 mL/20 mL) and then dried under atmospheric pressure at room temperature.

Workup

  1. additionis added, dropwise over 10 minutes
  2. customThe aqueous and organic phases are separated
  3. extractionthe aqueous phase is extracted with CH2Cl2 (twice 75 mL)
  4. washThe combined organic phases are washed with water (3 times 10 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationThe phases are concentrated to 100 mL under reduced pressure at room temperature
  7. addition50 mL of petroleum ether are added
  8. filtrationThe precipitate is filtered
  9. washwashed with CH2Cl2/petroleum ether (5 mL/10 mL
  10. customthen 0 mL/20 mL) and then dried under atmospheric pressure at room temperature

Sources & evidence

ORD record
ord-94cf2bcf799b416d82427b61b8391ece
Source dataset
uspto-grants-2016_07
Patent number
US09394380B2

Reaction notes

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